Abstract
The regiochemistry of the reaction of acetoacetic ester with vinylacetylene, isopropenylacetylene, and vinylisopropenylacetylene in the presence of the manganese acetate/copper acetate oxidative system was studied. Derivatives of furan and 4,5-dihydrofuran were obtained as a result of oxidative cyclization of intermediate radicals that contain unsaturated groups in the α position. Data from the IR, UV, PMR, 13C NMR, and mass spectra of the synthesized compounds are presented.
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A. A. Pashayan, S. A. Vorskanyan, Zh. A. Chobanyan, and Sh. O. Badanyan, Arm. Khim, Zh., 33, 133 (1980).
G. G. Melikyan, D. A. Mkrtchyan, and Sh. O. Badanyan, Khim. Geterotsikl. Soedin., No. 7, 884 (1980).
G. I. Niklshin and É. I. Troyanskii, Zh. Vses. Khim. Ova., No. 2, 169 (1979).
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Communication 75 from the series “Reactions of Unsaturated Compounds.” See [1] for Communication 74.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 19–23, January, 1982.
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Melikyan, G.G., Mkrtchyan, D.A. & Badanyan, S.O. Synthesis of 4,5-dihydrofuran derivatives by the reaction of acetoacetic ester with conjugated alkenynes. Chem Heterocycl Compd 18, 14–18 (1982). https://doi.org/10.1007/BF00513280
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DOI: https://doi.org/10.1007/BF00513280